Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-pent-4-enyloxy-tetrahydro-pyran-4-yl ester | 124771-17-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-pent-4-enyloxy-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-pent-4-enoxyoxan-2-yl]methyl acetate
• CAS: 124771-17-1
• 化学式: C₂₅H₂₉NO₁₀
• 分子量: 503.506
• InChiKey: HGFCOKYGLWYICW-ANOZEODCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-pent-4-enyloxy-tetrahydro-pyran-4-yl ester 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 4.0h， 生成 pent-4-enyl 2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Studies Related to Synthesis of Glycophosphatidylinositol Membrane-Bound Protein Anchors. 6. Convergent Assembly of Subunits

  摘要：

  Glycophosphatidylinositol anchors of membrane-bound proteins are thought to comprise a common pentasaccharide core containing mannan, glucosamine, and inositol residues. A synthetic route to this core is described. In addition, the complete heptasaccharide moiety of the rat brain Thy-1 membrane anchor, the first mammalian membrane anchor to be characterized, has been synthesized. In the case of the Thy-1 anchor, the synthetic plan is based on three building blocks comprising glucosamine-inositol, galactosamine-mannose, and trimannan residues. Although glycosyl donors other than n-pentenyl glycosides (NPGs) have been used in preparing each of these building blocks, the final assembly of the heptasaccharide utilizes NPGs as the only glycosyl donors. The mildness of the conditions for these coupling reactions has allowed us to make provisions for subsequent installation of the three phosphodiester units.

  DOI：

  10.1021/ja00110a011
• 作为产物：
  描述：

  4-戊烯-1-醇 、 在 trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-pent-4-enyloxy-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  金（I）催化的糖基邻炔基苯甲酸酯作为供体的糖基化：一般范围及其在环三萜皂苷合成中的应用

  摘要：

  糖基邻炔基苯甲酸酯已成为在金（I）配合物如Ph 3 PAuOTf和Ph 3 PAuNTf 2催化下进行糖苷化的新一代供体（Tf ＝三氟甲磺酸盐）。这些供体种类繁多，包括2-脱氧糖和唾液酸供体，易于制备且易于保存。与醇类的糖苷偶联收率通常非常好；即使与不良亲核酰胺直接偶联也能获得令人满意的收率。此外，已经实现了具有2-脱氧糖供体的出色的α-选择性糖基化和β-选择性唾液酸化。本糖基化方案在环状三萜四糖高效合成中的应用进一步证明了这种新方法的多功能性和有效性，因为已实现了羧酸的新型化学选择性糖基化和新的单锅顺序糖基化序列。

  DOI：

  10.1002/chem.200902548

文献信息

• An efficient glycosylation protocol with glycosyl ortho-alkynylbenzoates as donors under the catalysis of Ph3PAuOTf
  作者：Yao Li、You Yang、Biao Yu

  DOI：10.1016/j.tetlet.2008.04.017

  日期：2008.5

  A new and powerful glycosylation protocol with glycosyl ortho-alkynylbenzoates as donors and Ph3PAuOTf as a promoter is disclosed. The donors are readily available and stable; the glycosidic coupling yields are generally excellent; the promotion system is catalytic, neutral, and orthogonal to the known glycosylation conditions.

  公开了一种新的且功能强大的糖基化方案，其中糖基邻炔基苯甲酸酯为供体，Ph 3 PAuOTf为启动子。捐助者随时可用且稳定；糖苷偶联的产量通常是优异的；促进系统是催化的，中性的，并且与已知的糖基化条件正交。
• Synthesis of Nonracemic Allylic Hydroxy Phosphonates via Alkene Cross Metathesis
  作者：Anyu He、Bingli Yan、Anchalee Thanavaro、Christopher D. Spilling、Nigam P. Rath

  DOI：10.1021/jo0490090

  日期：2004.12.1

  their derivatives can be interconverted by using cross metathesis with second generation Grubbs catalyst. The absolute stereochemistry of the starting phosphonate is conserved in the product. Cross metathesis reaction of the acrolein-derived phosphonate 2a yields a series of functionalized allylic hydroxy phosphonates. However, the cross metathesis reaction is often accompanied by competing dimerization

  烯丙基羟基膦酸酯及其衍生物可通过与第二代Grubbs催化剂进行交叉复分解而相互转化。起始膦酸酯的绝对立体化学在产物中是保守的。丙烯醛衍生的膦酸酯2a的交叉复分解反应产生一系列官能化的烯丙基羟基膦酸酯。然而，交叉复分解反应通常伴随竞争性二聚化和烯烃迁移反应，从而导致产率降低。还检查了肉桂醛和巴豆醛衍生的膦酸酯2b和2c。通常，膦酸酯2b和2c的复分解反应比膦酸酯的复分解反应要慢得多。2a导致混合。膦酸酯2a的几种羟基保护衍生物（碳酸甲酯3a，乙酸酯4a，氨基甲酸N-甲苯磺酯5a，TBDMS 6a和乙酰乙酸酯7a）进行复分解而不会发生竞争性副反应，从而以高至优异的收率得到取代的烯丙基膦酸酯。
• Handlon, Anthony L.; Fraser-Reid, Bert, Journal of the American Chemical Society, 1993, vol. 115, # 9, p. 3796 - 3797
  作者：Handlon, Anthony L.、Fraser-Reid, Bert

  DOI：——

  日期：——
• n-Pentenyl 2-amino-2-deoxy glycosides undergo stereoselective coupling under mild, chemospecific conditions
  作者：David R. Mootoo、Bert Fraser-Reid

  DOI：10.1016/s0040-4039(01)80399-3

  日期：——
• MOOTOO, DAVID R.;FRASER-REID, BERT, TETRAHEDRON LETT., 30,(1989) N8, C. 2363-2366
  作者：MOOTOO, DAVID R.、FRASER-REID, BERT

  DOI：——

  日期：——